Water → HCID 9817035, compound

HRID 1084814Notes

Reaction equation

HRID 1084814 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[C:8]1([CH2:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]=2[OH:25])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O>N1C=CC=CC=1>[C:1]([O:25][C:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:23]=[CH:24][C:15]=1[CH2:14][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 160268Dup 654

Product 1

HCID 9817035HCID 9817035, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of acetic anhydride (3.27, 0.032 mol) in pyridine (50 mL) was stirred at 0°. 2-Phenylmethyl-1-naphthol (5.00 g, 0.021 mol) was added and the mixture was stirred while warming to room temperature. After 18 h, water was added and the mixture was extracted with ether. The ether phase was washed with dilute hydrochloric acid, then with water, then with brine and was dried over MgSO4. Concentration afforded a brown oil which was flash chromatographed (5% ethyl acetate/hexane). The resulting oil crystallized on standing and was recrystallized (hexane) to provide the title compound (4.75 g, 82%) as white needles: mp 67°-69°; NMR (CDCl3) 7.9-7.6 (m, 3H), 7.45 (m, 2H), 7.20 (m, 6H), 4.01 (s, 2H), 2.40 (s, 3H); IR (mull) 1760; Mass Spec (EI) 276 (9), 234 (100), 156 (20); Calcd. for C19H16O2;C-82.57 H-5.84., Found: C-82.66 H-5.93

Workup

  1. extractionthe mixture was extracted with ether
  2. washThe ether phase was washed with dilute hydrochloric acid
  3. dry with materialwith water, then with brine and was dried over MgSO4
  4. concentrationConcentration
  5. customafforded a brown oil which
  6. customchromatographed (5% ethyl acetate/hexane)
  7. customThe resulting oil crystallized
  8. customwas recrystallized (hexane)

Sources & evidence

ORD record
ord-2fbbf5bf88474b3b90f8b0a9d7410890
Source dataset
uspto-grants-1991_04
Patent number
US05006555

Reaction notes

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