Phosgene → Benzeneacetyl chloride, 4-(acetyloxy)-

HRID 39257

Reaction equation

HRID 39257 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15]O)=[CH:11][CH:10]=1)(=[O:7])[CH3:6]>C1(C)C=CC=CC=1>[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:1]([Cl:4])=[O:2])=[CH:11][CH:10]=1)(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 959064-Acetoxybenzyl alcohol

Product 1

HCID 182488Benzeneacetyl chloride, 4-(acetyloxy)-

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of phosgene in toluene (20% w/w, 2.2 mL, 4.2 mmol), cooled in an ice bath, was added dropwise a solution of 60 (321 mg, 1.9 mmol) in 2 mL of toluene. The mixture was stirred in the same bath, which was left to come to room temperature on its own. After 18 h, the mixture was concentrated in vacuo to give 61, which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ 2.30 (s, 3H), 5.28 (s, 2H), 7.13 (d, J=8.6 Hz, 2H), 7.42 (d, J=8.7 Hz, 2H).

Workup

  1. waitwas left
  2. customto come to room temperature on its
  3. concentrationthe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-92490217d32c40b8aa54f432ecaf61a4
Source dataset
uspto-grants-2013_09
Patent number
US08524691B2

Linked notes

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