Benzyl 4-Hydroxybenzoate → 4-[2-(4,4-Dimethyl-chroman-7-yl)-heptanoyloxy]-benzoic acid benzyl ester

HRID 899296Notes

Reaction equation

HRID 899296 reaction equation
[CH3:1][C:2]1([CH3:21])[C:11]2[C:6](=[CH:7][C:8]([CH:12]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:13]([OH:15])=[O:14])=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1.O[C:23]1[CH:38]=[CH:37][C:26]([C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])=[CH:25][CH:24]=1.C1CCC(N=C=NC2CCCCC2)CC1>ClCCl.CN(C1C=CN=CC=1)C>[CH2:30]([O:29][C:27](=[O:28])[C:26]1[CH:37]=[CH:38][C:23]([O:14][C:13](=[O:15])[CH:12]([C:8]2[CH:7]=[C:6]3[C:11]([C:2]([CH3:21])([CH3:1])[CH2:3][CH2:4][O:5]3)=[CH:10][CH:9]=2)[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:24][CH:25]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

6

Reactant 3

HCID 7180Benzyl 4-HydroxybenzoateHCID 10868DicyclohexylcarbodiimideHCID 226406782-(4,4-Dimethyl-chroman-7-yl)-heptanoic acid

Product 1

HCID 692169914-[2-(4,4-Dimethyl-chroman-7-yl)-heptanoyloxy]-benzoic acid benzyl esterYield 84.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(4,4-dimethyl-chroman-7-yl)-heptanoic acid (105 mg, 0.36 mmol) in 5 mL of dichloromethane with 91.6 mg, 0.4 mmol of benzyl 4-hydroxybenzoate and 44 mg, 0.36 mmol of DMAP was cooled to 0° C. and treated with 83 mg, 0.4 mmol of DCC. The mixture was kept at 0° C. for 15 minutes, then warmed to room temperature. After 2 h, the mixture was filtered and the resulting solution was washed with water and brine. The solution was dried and concentrated, then purified by flash chromatography (8% ethyl acetate/hexane) to give 152 mg (84%) of 4-[2-(4,4-dimethyl-chroman-7-yl)-heptanoyloxy]-benzoic acid benzyl ester.

Workup

  1. waitAfter 2 h
  2. filtrationthe mixture was filtered
  3. washthe resulting solution was washed with water and brine
  4. customThe solution was dried
  5. concentrationconcentrated
  6. custompurified by flash chromatography (8% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8bc5254178e24cc8900753035c32dad5
Source dataset
uspto-grants-2008_04
Patent number
US07354931B2

Reaction notes

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