HCID 14570910, compound → HCID 14570911, compound

HRID 1607283Notes

Reaction equation

HRID 1607283 reaction equation
[OH:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][C:7]2[O:8][C:9]3[C:16]([Cl:17])=[CH:15][C:14]([CH2:18][CH2:19][CH3:20])=[C:13]([OH:21])[C:10]=3[C:11]=2[CH3:12])=[CH:4][CH:3]=1>N1C=CC=CC=1.C(OC(=O)C)(=O)C>[C:2]([O:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][C:7]2[O:8][C:9]3[C:16]([Cl:17])=[CH:15][C:14]([CH2:18][CH2:19][CH3:20])=[C:13]([O:21][C:7](=[O:8])[CH3:6])[C:10]=3[C:11]=2[CH3:12])=[CH:4][CH:3]=1)(=[O:1])[CH3:3]

Participants

4

Reactant 1

HCID 14570910HCID 14570910, compound

Product 1

HCID 14570911HCID 14570911, compoundYield 176.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 2-(p-hydroxybenzyl)-3-methyl-4-hydroxy-5-propyl-7-chlorobenzofuran (1 gm; 3 mmoles) in pyridine (15 mL) and acetic anhydride (3 mL) was stirred at 50° C. for 15 minutes. The volatiles were removed in vacuo leaving a residue that crystallised on cooling. It was slurried with hexane, filtered, washed with hexane, and air dried to yield 1.1 gm (87%) of 2-(p-acetoxybenzyl)-3-methyl-4-acetoxy-5-propyl-7-chlorobenzofuran, mp. 119°-120° C.

Workup

  1. customThe volatiles were removed in vacuo
  2. customleaving a residue that
  3. customcrystallised
  4. temperatureon cooling
  5. filtrationfiltered
  6. washwashed with hexane, and air
  7. customdried

Sources & evidence

ORD record
ord-63cd6544a6174782ac150599dd30bef1
Source dataset
uspto-grants-1989_09
Patent number
US04863958

Reaction notes

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